Alternatived Products of [ 66154-69-6 ]
Product Details of [ 66154-69-6 ]
| CAS No. : | 66154-69-6 |
MDL No. : | MFCD14705772 |
| Formula : |
C7H6N2O2S
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : | 182.20 g/mol |
Pubchem ID : | - |
| Synonyms : |
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Safety of [ 66154-69-6 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 66154-69-6 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 66154-69-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
/BRN= 111968/, CH3SO2Cl, KCN, Acn., H2O; |
|
- 2
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[ 33252-30-1 ]
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[ 5188-07-8 ]
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[ 66154-69-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 58% |
Stage #1: 2-chloro-4-pyridinenitrile; sodium thiomethoxide In tetrahydrofuran at 50℃; for 2h;
Stage #2: With sodium perborate tetrahydrate; acetic acid In tetrahydrofuran at 55℃; for 16h; |
42
NaSMe (6.74 g, 90 wt.%, 1.2 eq) was charged to a flask followed by THF (10 niL). To the slurry was charged a solution of 2-chloro-4-cyanopyridine (10.0 g, 72.2 mmol, 1.0 eq) in THF (20 rnL). The reaction mixture was heated at 5O0C for 2 hours. The batch was then treated with NaBO3«4H2O (33.31 g, 3.0 eq) followed by AcOH (50 rnL). The reaction mixture was heated at 550C for 16 hours. The THF was distilled out under slight vacuum at 550C, and the resulting white slurry was treated with water (120 mL) and cooled to ambient temperature and held for 1 hour. The batch was filtered, the solid washed well with water, and then oven dried under vacuum to afford 2- (methylsulfonyl)isonicotinonitrile as a white solid, 7.65 g, >99.5 area % purity by HPLC, 58% yield. |
- 3
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[ 24424-99-5 ]
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[ 66154-69-6 ]
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[ 1220166-30-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 76% |
Stage #1: 4‐cyano‐2‐methylsulfonylpyridine With sodium tetrahydroborate; trifluoroacetic acid; zinc dibromide In tetrahydrofuran at 0 - 20℃;
Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran; methanol; water at 0 - 20℃; for 2h; |
42
2-(Methylsulfonyl)isonicotinonitrile (10.93 g, 60.0 mmol, 1.0 eq), NaBH4 (3.41 g, 90.0 mmol, 1.5 eq) and zinc bromide (1.35 g, 6.0 mmol, 0.1 eq) were charged to a 250 mL flask. THF (60 mL) was charged, and the slurry cooled to 0-50C. TFA (6.69 mL, 90.0 mmol, 1.5 eq) was charged at a rate to keep the temperature below 2O0C and to control hydrogen evolution. After the addition, the batch was stirred at ambient temperature for 1-2 hours. The reaction mixture was then cooled to 0-50C and treated with methanol (10 mL) followed by water (40 mL) and finally a solution of di-tert-buty dicarbonate (15.06 g, 69.0 mmol, 1.15 eq) in THF (10 mL). The batch was stirred at ambient temperature for 2 hours, and then the THF and MeOH was removed by distillation under vacuum at 550C. To the resulting slurry was added water (40 mL), toluene (20 mL) and heptane (40 mL). The slurry was stirred for 1 hour at ambient temperature and filtered. The solid was washed with water and heptane, and then oven dried under vacuum to afford tert- butyl (2-(methylsulfonyl)pyridin-4-yl)methylcarbamate as an off-white solid, 13.25 g, 97.9 wt.% purity, 76% yield. |
- 4
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[ 66154-69-6 ]
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(2-(methylsulfonyl)pyridin-4-yl)methanamine hydrochloride
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 82% |
Stage #1: 4‐cyano‐2‐methylsulfonylpyridine With hydrogen In methanol; water at 25℃; for 7h;
Stage #2: With hydrogenchloride In methanol; water; isopropyl alcohol for 18h; |
SYNTHETIC EXAMPLES
A hydrogenation vessel is charged with 2-(methanesulfonyl)-4-cyanopyridine (8.00 g, 43.9 mmol), 10 wt. % Pd/C (50% water) (800 mg, 0.377 mmol) and MeOH (48 mL). The mixture is hydrogenated under 100 psi of hydrogen at 25° C. for 7 hours. The reaction mixture is filtered to remove the catalyst, using MeOH to rinse, and the filtrate is concentrated to a volume of 24 mL. Isopropanol (48 mL) is added, followed by concentrated hydrochloric acid (4.03 mL, 48.3 mmol, 1.1 eq). The resulting slurry is stirred for 18 hours, filtered, and the resulting solid is washed with isopropanol and dried under vacuum. The product, 2-(methylsulfonyl)pyridin-4-yl)methanamine hydrochloride, is obtained as a solid (8.10 g, 82% yield) with no desulfonyl impurity by HPLC analysis, and with a residual Pd content of 46 ppm. |
- 5
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[ 66154-69-6 ]
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(2‐methylsulfonyl‐4‐pyridyl)‐ditritio‐methanamine hydrochloride
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With hydrogenchloride; tritium; palladium on activated charcoal In methanol; water for 20h; |
|
Reference：
[1]Latli, Bachir; Hrapchak, Matt; Cheveliakov, Maxim; Reeves, Jonathan T.; Marsini, Maurice; Busacca, Carl A.; Senanayake, Chris H.
[Journal of labelled compounds and radiopharmaceuticals, 2018, vol. 61, # 10, p. 764 - 772]
- 6
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[ 33252-30-1 ]
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[ 20277-69-4 ]
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[ 66154-69-6 ]
| Yield | Reaction Conditions | Operation in experiment |
| 78% |
In 1-methyl-pyrrolidin-2-one at 125℃; for 14h; |
|
Reference：
[1]Latli, Bachir; Hrapchak, Matt; Cheveliakov, Maxim; Reeves, Jonathan T.; Marsini, Maurice; Busacca, Carl A.; Senanayake, Chris H.
[Journal of labelled compounds and radiopharmaceuticals, 2018, vol. 61, # 10, p. 764 - 772]
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